Sodium hydride → 6-Methoxy-1-methyl-3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide

HRID 1244040Notes

Reaction equation

HRID 1244040 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N:11]([CH3:16])[S:12]([CH3:15])(=[O:14])=[O:13].[H-].[Na+]>CN(C=O)C>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][C:4]2[N:11]([CH3:16])[S:12](=[O:14])(=[O:13])[CH2:15][CH2:2][C:3]=2[CH:8]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21931771N-(2-Bromomethyl-4-methoxy-phenyl)-N-methyl-methanesulfonamide

Product 1

HCID 219317126-Methoxy-1-methyl-3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxideYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 291 mg (0.95 mmol) N-(2-Bromomethyl-4-methoxy-phenyl)-N-methyl-methanesulfonamide in 15 ml of DMF was treated with 45 mg (1.14 mmol) 60% NaH and the reaction mixture was stirred at 75° C. for 4 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, dried and evaporated. The residue was passed through a short plug of silica gel eluting with 25% ethyl acetate in hexane. There was obtained 123 mg (57%) of the desired product. Mass spectrum APCI (m/z) 228 (p+1).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-835bd49c2d69414fab553123461ce7b9
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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